Novel liquid crystalline compound having a 1,1,2,3,3,3,-hexafluoropropyl group and liquid crystal composition

Abstract: A liquid crystalline compound expressed by the formula (1) (wherein R₁ is an alkyl group of 1-12C, and one CH₂ group or two CH₂ groups not adjacent to each other in the alkyl group may be substituted by substituent(s) selected from among 0 atom, -CO- group, -O-CO- group, -CO-O- group and -CH=CH- group; X is covalent bond, -CH₂CH₂-, -CH=CH-, -C≡C-, -CH₂O-, -OCH₂-, -CO-O- or -O-CO-; Y₁ and Y₂ each independently are H, F, Cℓ or methyl group; rings A, B and C each independently are benzene ring or cyclohexane ring, and may be substituted by halogen atom(s) or a methyl group(s); and ℓ, m, n and p each independently are 1 or 2 and ℓ+m is one or more) and a liquid crystal composition using the same, are provided, which liquid crystal composition has a large Δn, a low viscosity and a high voltage retention and exhibits a nematic liquid crystal phase within a broad temperature range, and further has a very high Δε and a low driving voltage and is useful for use for TFT.

Description: 1. Field of the Invention This invention relates to liquid crystalline compounds and liquid crystal compositions. More particularly, it relates to novel liquid crystalline compounds having a hexafluoropropyl group and liquid crystal compositions containing the same. 2. Description of the Related Art Liquid crystal compositions, particularly nematic liquid crystal compositions, have been broadly used for various display materials such as displays for watches, electronic calculators, word processors, computer terminals or television, etc. Liquid crystal display elements using nematic liquid crystal compositions have three kinds of main driving modes of twisted nematic (hereinafter abbreviated to TN) mode, super-twisted nematic (hereinafter abbreviated to STN) mode and thin-film transistor drive mode (hereinafter abbreviated to TFT). Among these, TFT mode has a superior display capability; hence it has been used for televisions and large scale color display and broadening of its use applications has been most expected. Liquid crystal compounds for TFT require the following characteristics of: 1) exhibiting nematic liquid crystal phase within a broad temperature range; 2) having a large dielectric anisotropy value (herein-after abbreviated to ▵ε); 3) having a large optical anisotropy value (hereinafter abbreviated to ▵n); 4) having a low viscosity; and 5) having a high voltage holding ratio (abbreviated hereinafter to VHR). Various compounds have been proposed for satisfying these characteristics. As compounds having a high VHR, compounds containing fluorine atoms are superior, and research for liquid crystal compounds containing fluorine atoms has been extensively carried out. For example, compounds having 3,4-difluorobenzene core at the terminal of the molecule (DE 3042391), and compounds having 3,4,5-trifluorobenzene core aiming at a larger Δε (USP 5032313) have been known, but they are unsuitable due to their very low clearing points. Further, compounds having introduced trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group at the terminal of the molecules (DE 4027840) have been known, but they have drawbacks that the clearing point is still low and the An is still small. Further, in recent years, a compound having 1,1,2,2-tetrafluoroethoxy group at its terminal (DE 4142519) and a compound having 2,2,2-tri-fluoroethoxy group at its terminal (WO 93/3113) have been reported, but they have drawbacks that their clearing points are low and moreover have no sufficiently large Δε; hence they are insufficient in the aspects of characteristics. In order to obtain a compound exhibiting a larger Δε, an example of a compound having introducing a cyano group having a large dipole moment has been reported (Japanese patent application laid-open Nos. Sho 62-103057 and Sho 63-216858), but the viscosity not only increases, but also the VHR lowers; thus it was difficult to use them as liquid crystal compounds for TFT. Berichte der Bunsengesellschaft, Physikalische Chemie, vol. 97, no 10, October 1993, pages 1349-1355 describes liquid crystals with fluorine-containing alkyl groups, and indicates that the paper was presented at the 92nd Annual Meeting of the Deutsche Bunsen-Gesellschaft Für Physikalische Chemie in May 1993. SUMMARY OF THE INVENTION In order to solve the above problems, the present inventors have made extensive research, for providing liquid crystal compounds exhibiting a nematic liquid crystal phase within a broad temperature range and having a large ▵ε and ▵n, a low viscosity and a high VHR, and as a result, have completed the present invention. The present invention resides in the following aspects. (1) A liquid crystalline compound expressed by the formula (1) wherein R 1 represents an alkyl group of 1 to 12 carbon atoms and one CH 2 group or two CH 2 groups not adjacent to each other in the alkyl group may be replaced by group(s) selected from among oxygen atom, -CO-group, -O-CO- group, -CO-O- group and -CH=CH- group; X represents a covalent bond, -CH 2 CH 2 -, -CH=CH-, -C=C-, -CH 2 O- , -OCH 2 -, -CO-O- or -O-CO-; Y 1 and Y 2 each independently represent hydrogen atom, fluorine atom, chlorine atom or methyl group; rings A, B and C each independently represent a benzene ring or a cyclohexane ring and these rings may be substituted by a halogen atom(s) or a methyl group(s): and ℓ, m, n and p each independently represent 1 or 0, but ℓ+m is one or more,* (2) A liquid crystalline compound according to item (1), wherein R 1 represents an alkyl group of 1 to 12 carbon atoms and one CH 2 group or two CH 2 groups thereof not adjacent to each other in the alkyl group may be replaced by oxygen atom or -CH 2 =CH- group; X represents a covalent bond, -CH 2 CH 2 - or -C=C-; and Y 1 and Y 2 each independently represent hydrogen atom or fluorine atom. (3) A liquid crystalline compound according to item (2), wherein the R 1 represents an alkyl group of 1 to 12 carbon atoms. (4) A liquid crystalline compound according to item (3), wherein the ring C represents a benzene ring or a benzene ring substituted by halogen atom or methyl group. (5) A liquid crystalline compound according to item (3), wherein the ring C represents a cyclohexane ring or a cyclohexane ring substituted by halogen atom or methyl group. (6) A liquid crystalline compound according to item (2), wherein the R 1 represents an alkyl group of 1 to 12 carbon atoms and one CH 2 group or two CH 2 groups not adjacent to each other in the alkyl group is replaced by oxygen atom. (7) A liquid crystalline compound according to item (6), wherein the ring C represents benzene ring or a benzene ring substituted by halogen atom or methyl group. (8) A liquid crystalline compound according to item (6), wherein the ring C represents cyclohexane ring or a cyclohexane ring substituted by halogen atom or methyl group. (9) A liquid crystal composition comprising at least two components at least one of which is a liquid crystalline compound set forth in any one of items (1) to (8). DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS The liquid crystalline compound expressed by the formula (1) of the present invention is characterized by having a group expressed by the following formula at the terminal of the molecule; wherein Y 1 , Y 2 and p are as defined above. Hereinafter the above formula will be referred to as Q. This Q more concretely includes the following six groups: 3,5-disubstituted-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl group, 3-substituted-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl group, 4-(1,1,2,3,3,3-hexafluoro-propoxy)phenyl group, 3,5-disubstituted-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl group, 3-substituted-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl group, and 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl group. The liquid crystalline compound expressed by the formula (1) of the present invention characteristically having the Q is roughly classified in accordance with the kind of X in the formula, as follows: In the case where X in the formula represents a covalent bond, R 1 -Cy-Q R 1 -Ph-Q R 1 -Cy-Cy-Q R 1 -Cy-Ph-Q R 1 -Ph-Cy-Q R 1 -Ph-Ph-Q R 1 -Cy-Cy-Cy-Q R 1 -Cy-Cy-Ph-Q R 1 -Cy-Ph-Cy-Q R 1 -Ph-Cy-Cy-Q R 1 -Cy-Ph-Ph-Q R 1 -Ph-Cy-Ph-Q R 1 -Ph-Ph-Cy-Q R 1 -Ph-Ph-Ph-Q In the case of X = -CH 2 CH 2 -. R 1 -Cy-CH 2 CH 2 -Q R 1 -Ph-CH 2 CH 2 -Q R 1 -Cy-CH 2 CH 2 Cy-Q R 1 -Cy-CH 2 CH 2 -Ph-Q R 1 -Ph-CH 2 CH 2 -Cy-Q R 1 -Ph-CH 2 CH 2 -Ph-Q R 1 -Cy-Cy-CH 2 CH 2 -Q R 1 -Cy-Ph-CH 2 CH 2 -Q R 1 -Ph-Cy-CH 2 CH 2 -Q R 1 -Ph-Ph-CH 2 CH 2 -Q R 1 -Cy-Cy-CH 2 CH 2 -Cy-Q R 1 -Cy-Cy-CH 2 CH 2 -Ph-Q R 1 -Cy-Ph-CH 2 CH 2 -Cy-Q R 1 -Ph-Cy-CH 2 CH 2 -Cy-Q R 1 -Cy-Ph-CH 2 CH 2 -Ph-Q R 1 -Ph-Cy-CH 2 CH 2 -Ph-Q R 1 -Ph-Ph-CH 2 CH 2 -Cy-Q R 1 -Ph-Ph-CH 2 CH 2 -Ph-Q In the case of X = -CH=CH-, R 1 -Cy-CH=CH-Q R 1 -Ph-CH=CH-Q R 1 -Cy-CH=CH-Cy-Q R 1 -Cy-CH=CH-Ph-Q R 1 -Ph-CH=CH-Cy-Q R 1 -Ph-CH=CH-Ph-Q R 1 -Cy-Cy-CH=CH-Q R 1 -Cy-Ph-CH=CH-Q R 1 -Ph-Cy-CH=CH-Q R 1 -Ph-Ph-CH=CH-Q R 1 -Cy-Cy-CH=CH-Cy-Q R 1 -Cy-Cy-CH=CH-Ph-Q R 1 -Cy-Ph-CH=CH-Cy-Q R 1 -Ph-Cy-CH=CH-Cy-Q R 1 -Cy-Ph-CH=CH-Ph-Q R 1 -Ph-Cy-CH=CH-Ph-Q R 1 -Ph-Ph-CH=CH-Cy-Q R 1 -Ph-Ph-CH=CH-Ph-Q In the case of X = -C≡C-, R 1 -Cy-C≡C-Q R 1 -Ph-C≡C-Q R 1 -Cy-C≡C-Cy-Q R 1 -Cy-C≡C-Ph-Q R 1 -Ph-C≡C-Cy-Q R 1 -Ph-C≡C-Ph-Q R 1 -Cy-Cy-C≡C-Q R 1 -Cy-Ph-C≡C-Q R 1 -Ph-Cy-C≡C-Q R 1 -Ph-Ph-C≡C-Q R 1 -Cy-Cy-C≡C-Cy-Q R 1 -Cy-Cy-C≡C-Ph-Q R 1 -Cy-Ph-C≡C-Cy-Q R 1 -Ph-Cy-C≡C-Cy-Q R 1 -Cy-Ph-C≡C-Ph-Q R 1 -Ph-Cy-C≡C-Ph-Q R 1 -Ph-Ph-C≡C-Cy-Q R 1 -Ph-Ph-C≡C-Ph-Q In the case of X = -CH 2 O-, R 1 -Cy-CH 2 O-Q R 1 -Ph-CH 2 O-Q R 1 -Cy-CH 2 O-Cy-Q R 1 -Cy-CH 2 O-Ph-Q R 1 -Ph-CH 2 O-Cy-Q R 1 -Ph-CH 2 O-Ph-Q R 1 -Cy-Cy-CH 2 O-Q R 1 -Cy-Ph-CH 2 O-Q R 1 -Ph-Cy-CH 2 O-Q R 1 -Ph-Ph-CH 2 O-Q R 1 -Cy-Cy-CH 2 O-Cy-Q R 1 -Cy-Cy-CH 2 O-Ph-Q R 1 -Cy-Ph-CH 2 O-Cy-Q R 1 -Ph-Cy-CH 2 O-Cy-Q R 1 -Cy-Ph-CH 2 O-Ph-Q R 1 -Ph-Cy-CH 2 O-Ph-Q R 1 -Ph-Ph-CH 2 O-Cy-Q R 1 -Ph-Ph-CH 2 O-Ph-Q In the case of X = -OCH 2 -, R 1 -Cy-OCH 2 -Q R 1 -Ph-OCH 2 -Q R 1 -Cy-OCH 2 -Cy-Q R 1 -Cy-OCH 2 -Ph-Q R 1 -Ph-OCH 2 -Cy-Q R 1 -Ph-OCH 2 -Ph-Q R 1 -Cy-Cy-OCH 2 -Q R 1 -Cy-Ph-OCH 2 -Q R 1 -Ph-Cy-OCH 2 -Q R 1 -Ph-Ph-OCH 2 -Q R 1 -Cy-Cy-OCH 2 -Cy-Q R 1 -Cy-Cy-OCH 2 -Ph-Q R 1 -Cy-Ph-OCH 2 -Cy-Q R 1 -Ph-Cy-OCH 2 -Cy-Q R 1 -Cy-Ph-OCH 2 -Ph-Q R 1 -Ph-Cy-OCH 2 -Ph-Q R 1 -Ph-Ph-OCH 2 -Cy-Q R 1 -Ph-Ph-OCH 2 -Ph-Q In the case of X = -CO-O-, R 1 -Cy-CO-O-Q R 1 -Ph-CO-O-Q R 1 -Cy-CO-O-Cy-Q R 1 -Cy-CO-O-Ph-Q R 1 -Ph-CO-O-Cy-Q R 1 -Ph-CO-O-Ph-Q R 1 -Cy-Cy-CO-O-Q R 1 -Cy-Ph-CO-O-Q R 1 -Ph-Cy-CO-O-Q R 1 -Ph-Ph-CO-O-Q R 1 -Cy-Cy-CO-O-Cy-Q R 1 -Cy-Cy-CO-O-Ph-Q R 1 -Cy-Ph-CO-O-Cy-Q R 1 -Ph-Cy-CO-O-Cy-Q R 1 -Cy-Ph-CO-O-Ph-Q R 1 -Ph-Cy-CO-O-Ph-Q R 1 -Ph-Ph-CO-O-Cy-Q R 1 -Ph-Ph-CO-O-Ph-Q In the case of X = -O-CO-, R 1 -Cy-O-CO-Q R 1 -Ph-O-CO-Q R 1 -Cy-O-CO-Cy-Q R 1 -Cy-O-CO-Ph-Q R 1 -Ph-O-CO-Cy-Q R 1 -Ph-O-CO-Ph-Q R 1 -Cy-Cy-O-CO-Q R 1 -Cy-Ph-O-CO-Q R 1 -Ph-Cy-O-CO-Q R 1 -Ph-Ph-O-CO-Q R 1 -Cy-Cy-O-CO-Cy-Q R 1 -Cy-Cy-O-CO-Ph-Q R 1 -Cy-Ph-O-CO-Cy-Q R 1 -Ph-Cy-O-CO-Cy-Q R 1 -Cy-Ph-O-CO-Ph-Q R 1 -Ph-Cy-O-CO-Ph-Q R 1 -Ph-Ph-O-CO-Cy-Q R 1 -Ph-Ph-O-CO-Ph-Q In the above formulas, R 1 and Q are as defined above; Cy represents a cyclohexane ring substituted by halogen atom or methyl group or not substituted; and Ph represents a benzene ring substituted by halogen atom or methyl group or not substituted. Among these, concrete examples of liquid crystal compounds having particularly superior characteristics, namely those exhibiting a nematic liquid crystal phase within a broad temperature range, and having a large ▵ε and ▵n, a low viscosity and a high VHR, are the following (1aa-a) to (1hh-a): In these formulas, R 1 , Y 1 and and Y 2 each are as defined above, and Z 1 , Z 2 T 1 and T 2 each independently represent halogen atom or methyl group. Any of the compounds expressed by the formula (1) can form the components constituting a liquid crystal composition having superior characteristics, and if a composition having a particularly high clearing point is required, it is preferred to select a tricyclic compound and a tetracyclic compound, while if a composition having a somewhat low clearing point is required, it is preferred to select a bicydic compound. 1,1,2,3,3,3-Hexafluoropropoxy group and 1,1,2,3,3,3-hexafluoropropyl group have a capability of exhibiting a large ▵ε, by themselves. However, if a larger Δε is required, it is preferred that at least one of Z 1 , Z 2 , Y 1 , Y 2 , T 1 and T 2 be halogen atom or X be -CO-O-. If a larger An is required, a compound containing a plurality of benzene rings or a compound of X = -C≡C- is preferred. Since the compound of the present invention has a core containing no group raising the viscosity, such as cyano group, any of the compounds have a low viscosity, but if a further lower viscosity is required, the problem can be solved by selecting a compound containing a plurality of hexane rings. As described above, when Z 1 , Z 2 , X, Y, T 1 , T 2 and ring core are suitably selected, it is possible to optionally obtain compounds having required values of physical properties. The compound expressed by the formula (1) of the present invention can be prepared according to the process expressed by the following equations, depending upon the kind of X: In the above equations, L represents a halogeno-magnesium or halogenolithium; S represents chlorine atom, bromine atom or iodine atom; Y, R 1 , ℓ, m, n, p, rings A, B and C are as defined above. These compounds can be prepared according to Negishi et al's method (Journal of the Organic Chemistry, 42 , 1821 (1977), ditto 43 , 358 (1978)). Namely, zinc chloride is reacted with a Grignard reagent or lithium compound (2) prepared from the corresponding halide in a conventional manner to obtain a zinc derivative (3), followed by reacting this compound with a 3,5-di-substituted-4-(1,1,2,3,3,3-hexafluoropropoxy)halogenobenzene, a 3-substituted-4-(1,1,2,3,3,3-hexafluoropropoxy)halogenobenzene, a 4-(1,1,2,3,3,3-hexafluoropropoxy)halogenobenzene, a 3,5-disubstituted-4-(1,1,2,3,3,3-hexafluoropropyl)halogenobenzene, a 3-substituted-4-(1,1,2, 3,3,3-hexafluoropropyl)halogenobenzene or a 4-(1,1,2,3,3,3-hexafluoropropyl)halogenobenzene (4), in the presence of a catalyst, to carry out cross-coupling reaction, thereby obtaining the compounds (1aa) to (1 an). As the catalyst used, a zero valence palladium catalyst is preferable. Further, the compounds (1 aa) to (1 an) can also be prepared according to the method of Luche et al. (Journal of the Organic Chemistry, 48 , 3837 (1983) or Tetrahedron Letters, 25 , 3463 (1984)). Namely, zinc bromide is reacted with a halide (6) under irradiation of ultrasonic wave to obtain a zinc derivative (7), followed by reacting (4) with (7) in the presence of a catalyst to carry out a cross-coupling reaction, to obtain the compounds (1aa) to (1an). As the catalyst used, a divalent palladium catalyst is preferable. Further, it is also possible to prepare the compounds by reacting 1,1,2,3,3,3-hexafluoropropyl iodide or 1,1,2,3,3,3-hexafluoropropyl bromide (10) with a phenol (9) under pressure. Further, the above Grignard reagent (2) is easily converted into a boric acid compound, and this compound can be derived into (1aa) to (1 an) according to Miller et al's method (Organometallics, 3 , 1261 (1984)). In the above equations, L, S, Y 1 , Y 2 , R 1 , ℓ, m, n, p, rings A, B and C are as defined above. In the case of n=0, zinc bromide is reacted with a halogen compound (11), as described above, followed by reacting a halogenobenzene (4) with the thus obtained zinc compound (12) in the presence of a catalyst, to prepare the compounds (1ba), (1bb), (1bg) to (1bj). On the other hand, in the case of n=1, in the same manner as above, a Grignard reagent, a lithium compound (13) or a halide (15) is respectively converted into the corresponding zinc derivative (14) or (16), followed by reacting a halogenobenzene (4) in the presence of a catalyst (5) or (8), to prepare the compounds (1bc) to (1bf) and the compounds (1bk) to (1br). Further, even when a halide (10) is reacted with a phenol (17), it is possible to prepare the compounds (1ba) to (1br). In the above equations, L, S, Y 1 , Y 2 , R 1 , ℓ, m, n, p and rings A, B and C are as defined above. In the case of n=0, in the same manner as above, zinc bromide is reacted with a halogen compound (18), followed by reacting a halogenobenzene (4) with the thus obtained zinc derivative (19) in the presence of a catalyst, to prepare compounds (1ca), (1cb), (1cg) to (1cj). On the other hand, in the case of n=1, in the same manner as above, a Grignard reagent, a lithium compound (20) or a halide (22) is respectively converted into the corresponding zinc derivatives (21) or (23), followed by reacting a halogenobenzene (4) in the presence of a catalyst (5) or (8), to obtain compounds (1cc) to (1cf) and (1ck) to (1cr). In the above equations, L, S, Y 1 , Y 2 , R 1 , ℓ, m, n, p and rings A, B and C are as defined above. In the case of n=0, in the same manner as above, zinc chloride is reacted with a Grignard reagent or a lithium compound (24), followed by reacting (4) with the thus obtained zinc derivative (25) in the presence of a catalyst (5), to obtain compounds (1da), (1db), (1dg) to (1dj). On the other hand, in the case of n=1, in the same manner as above, a Grignard reagent, a lithium compound (26) or a halide (28) is respectively converted into the corresponding zinc derivative (27) or (29), followed by reacting a halogenobenzene (4) in the presence of a catalyst (5) or (8), to prepare compounds (1dc) to (1df). In the equations, S, Y 1 , Y 2 , R 1 , ℓ, m, n, p and rings A, B and C are as defined above. When sodium hydride and then a halide (30) are reacted with an alcohol or phenol (31), it is possible to prepare compounds (1ea) to (1er). In addition, (31) can be prepared by reacting a phenol (32) with a halide (10) in the same manner as above. Further, even when (30) is reacted with (32) and a halide (10) is reacted with the resulting phenol (33) in the same manner as above, compounds (1ea) to (1er) can be prepared. In the above equations, S, Y 1 , Y 2 , R 1 , ℓ, m, n, p and rings A, B and C are as defined above. When sodium hydride and then a chloride (35) are reacted with an alcohol or a phenol (34) and a halide (10) is reacted with the resulting phenol (36), compounds (1fa) to (1fr) can be prepared in the same manner as above. wherein R 1 , ℓ, m and rings A and B are as defined above. When a carboxylic acid (37) and an alcohol or a phenol (31) are subjected to dehydration-condensation, compounds (1ga) to (1gr) can be prepared. In the above equations, R 1 , ℓ, m, n, p and rings A, B and C are as defined above. When a carboxylic acid (38) and an alcohol or phenol (34) are subjected to dehydration-condensation, to obtain a phenol (39), followed by reacting a halide (10) with the phenol, it is possible to prepare compounds (1ha) to (1hr). In addition, a compound of p=1 among compound (4) can be prepared from a 4-hydroxyhalogenobenzene and 1,1,2,3,3,3-hexafluoropropyl bromide or 1,1,2,3,3,3-hexafluoropropyl iodide (these propyl bromide or propyl iodide being collectively abbreviated to HFPs) or hexafluoropropene, according to the method described in Bulletine Society Chemistry of France, 923 (1974), for example. At that time, since HFPs as the raw material have a low boiling point, it is preferred to carry out the reaction in an autoclave under pressure in order to improve the reactivity. Further, a compound of p=0 among compound (4), can be prepared by reacting a HFPs with a phenyllithium derivative to carry out a coupling reaction. The thus obtained compound (1) of the present invention is far superior as a constituting component of nematic liquid crystal compositions. Namely, since the compound easily mixes with various liquid crystal compounds, besides they have the above described superior characteristics, it is possible to provide nematic liquid crystal compositions suitable to electrooptical elements. Such liquid crystal compositions can be obtained preferably by blending a component (A) containing at least one kind of the compound (1) and besides, compounds optionally selected in accordance with objects, from a group of compounds (B) having a ▵ε ≧ 5, a group of compounds (C) having a |▵ε|<5, a group of compounds (D) having particularly a clearing point of 80°C or higher and another group of compounds (E). As compounds included in (B), (C), (D) and (E), the following compounds can be preferably exemplified: Namely, as compounds included in (B), the following (B1) to (B13) can be exemplified: In the above formulas, Ra represents an alkyl group or alkenyl group having 1 to 10 carbon atoms, but one carbon atom or two or more not adjacent carbon atoms in the groups may be replaced by oxygen atom. Further, as compounds corresponding to (C), the following (C1) to (C37) can be exemplified: In the above formulas, Ra and Ra' each independently represent an alkyl group or alkenyl group having 1 to 10 carbon atoms, but one carbon atom or two or more not adjacent carbon atoms may be replaced by oxygen atom. Further, as compounds included in (D), the following compounds (D1) to (D57) can be exemplified. In the above formulas, Ra and Ra' are as defined above. Further, as compounds included in (E), the following (E1) to (E22) can be exemplified. In the above formulas, Ra and Ra' are as defined above. The liquid crystal composition of the present invention is preferred in that when one kind or more of compounds expressed by the formula (1) are contained therein in a proportion of 0.1 to 40% by weight, as the composition has superior liquid crystal characteristics. Further, as nematic liquid crystal composition containing the compound of the present invention, composition examples mentioned below can be exemplified. In addition, compound Nos. are the same as those shown in Examples mentioned later. Hereinafter, 1,4-cyclohexylene and 1,2-ethenylene in side chains or central linkages refer to transconformation. Composition example 1 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-propylcyclohexyl)biphenyl(compound No. 1) 5% 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-pentylcyclohexyl)biphenyl(compound No. 17) 5% 2-fluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 1,2,3-trifluoro-5-(4-heptylcyclohexyl)benzene 9% 1,2-difluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 5% 1,2-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1,2-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 5% 1,2,3-trifluoro-5-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 7% 1,2,3-trifluoro-5-(4-(2-(4-butylcyclohexyl)ethyl)cyclohexyl)benzene 7% 1,2,3-trifluoro-5-(4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl)benzene 6% 1,2,3-trifluoro-5-(4-(4-propylcyclohexyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4-(4-butylcyclohexyl)cyclohexyl)benzene 5% 1,2,3-trifluoro-5-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl)benzene 11% 1,2,3-trifluoro-5-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethyl)benzene 10% Composition example 2 2',6'-difluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 47) 5% 2',6'-difluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 49) 5% 2',6'-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2',6'-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4-(4-propylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene(compound No. 91) 5% 4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene(compound No. 98) 5% 1,2,3-trifluoro-5-(4-heptylcyclohexyl)benzene 6% 1,2,3-trifluoro-5-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4-(2-(4-butylcyclohexyl)ethyl)cyclohexyl)benzene 9% 1,2,3-trifluoro-5-(4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4-(4-propylcyclohexyl)cyclohexyl-benzene 10% 1,2,3-trifluoro-5-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl)benzene 5% 1,2,3-trifluoro-5-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethylbenzene 5% 3,4,5-trifluoro-4'-(4-propylcyclohexyl)bipheny) 10% 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)biphenyl 5% Composition example 3 4-propylcyclohexyl-1-(1,1,2,3,3,3-hexafluoropropyl)benzene(compound No. 92) 10% 4-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene (compound No. 200) 10% 4-(4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene (compound No. 202) 10% 1,2,3-trifluoro-5-(4-(4-propylcyclohexyl)cyclohexyl-benzene 10% 1,2,3-trifluoro-5-(4-(4-butylcyclohexyl)cyclohexyl)benzene 5% 1,2,3-trifluoro-5-(2-(4-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(2-(4-(4-pentylcyclohexyl)ethyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl)benzene 10% 1,2,3-trifluoro-5-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethyl)benzene 10% 3,4,5-trifluoro-4'-(4-propylcyclohexyl)biphenyl 8% 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)biphenyl 7% Composition example 4 4'-(4-propylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(4-pentylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 191) 5% 2,6-difluoro-4-(4-propylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2,6-difluoro-4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 1,2,3-trifluoro-5-(2-(4-pentylcyclohexyl)ethyl)benzene 4% 4-fluorophenyl 4-pentylcyclohexanecarboxylate 9% 4-fluorophenyl 4-heptylcyclohexanecarboxylate 9% 1-methyl-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 6% 1,2-difluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 8% 1,2-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 8% 1,2-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 7% 1,2-difluoro-4'-(4-ethylcyclohexyl)biphenyl 6% 1,2-difluoro-4'-(4-propylcyclohexyl)biphenyl 6% 1,2-difluoro-4'-(4-pentylcyclohexyl)biphenyl 12% Composition example 5 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(4-pentylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4-(4-propylcyclohexyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene(compound No. 110) 5% 4-(4-(4-pentylcyclohexyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene(compound No. 111) 5% 2-fluoro-4-(4-propylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 1,2-difluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 10% 1,2-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 10% 1,2-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4.(4-ethylcyclohexyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4.(4-pentylcyclohexyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(4-(2-(4-ethylcyclohexyl)ethyl)cyclohexyl)benzene 10% 1,2,3-trifluoro-5-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl)benzene 10% Composition example 6 2'-fluoro-4'-(4-propylcyclohexyl)-4-1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 34) 5% 2'-fluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 36) 5% 4'-(4-propylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 28) 5% 4'-(4-pentylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 29) 5% 1-chloro-4-(4-propylcyclohexyl)benzene 5% 1-chloro-4-(4-pentylcyclohexyl)benzene 5% 1-chloro-4-(4-heptylcyclohexyl)benzene 5% 1,2-difluoro-4-(4-(2-(4-ethylcyclohexyl)ethyl)cyclohexyl)benzene 12% 1,2-difluoro-4-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 6% 1,2-difluoro-4-(4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl)benzene 12% 1-chloro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 5% 1-chloro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1-chloro-4-(4-(4-butylcyclohexyl)cyclohexyl)benzene 5% 1-chloro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 5% 1-chloro-2-fluoro-4-(4-(2-(4-ethylcyclohexyl)ethyl)cyclohexyl)benzene 6% 1-chloro-2-fluoro-4-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 5% 1-chloro-2-fluoro-4-(4-(2-(4-butylcyclohexyl)ethyl)cyclohexyl)benzene 5% Composition example 7 (for comparison purposes) 2-fluoro-4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(2-(4-(4-pentylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4'-ethyl-4-cyanobiphenyl 7% 4'-butyl-4-cyanobiphenyl 4% 1-cyano-4-(4-ethylcyclohexyl)benzene 12% 1-cyano-4-(4-propylcyclohexyl)benzene 3% 2-(3,4-difluorophenyl)-5-propylpyrimidine 6% 1-propyl-4-(4-methoxymethylcyclohexyl)cyclohexane 6% 1-pentyl-4-(4-methoxymethylcyclohexyl)cyclohexane 5% 1-methyl-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 4% 1-methyl-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1-fluoro-4-(4-(4-propylcyclohexyl)cydohexyl)benzene 4% 1-methoxy-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 4% 1-propyl-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 11% 1-cyano-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 8% 4-fluorophenyl 4-(4-propylcyclohexyl)benzoate 6% Composition example 8 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 267) 5% 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 283) 5% 4-(2-(4-(4-pentylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 285) 5% 2-(3,4-difluorophenyl)-5-pentylpyrimidine 13% 1-cyano-2-fluoro-4-ethylcyclohexyl)benzene 5% 1-cyano-2-fluoro-4-(4-propylcyclohexyl)benzene 8% 4'-ethyl-4-cyanobiphenyl 5% 1-cyano-4-(4-propylcyclohexyl)benzene 2% 1-cyano-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 6% 1-cyano-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 6% 1-cyano-4-(4-(4-butylcyclohexyl)cyclohexyl)benzene 6% 1-cyano-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 6% 1-methyl-4-(4(-4-propylcyclohexyl)cyclohexyl)benzene 5% 1-cyano-2-fluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 6% 1-cyano-2-fluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 6% 2-(4'-fluorobiphenyl)-5-propylpyrimidine 5% 2-(4'-fluorobiphenylyl)-5-butylpyrimidine 5% Composition example 9 2,6-difluoro-4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2,6-difluoro-4-(2-(4-4-pentylcycloheyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 283) 5% 1-cyano-4-(4-(3-butenyl)cyclohexyl)benzene 8% 1-cyano-4-(4-(3-pentenyl)cyclohexyl)benzene 7% 1-cyano-4-(4-propylcyclohexyl)benzene 7% 1-methyl-4-(2-(4-ethylphenyl)ethynyl)benzene 5% 1-methyl-4-(2-(4-hexylphenyl)ethynyl)benzene 10% 1-butyl-4-(2-(4-butylphenyl)ethynyl)benzene 5% 1-methoxy-4-(2-(4-ethylphenyl)ethynyl)benzene 11% 2-(4'-fluorobiphenylyl)-5-propylpyrimidine 6% 2-(4'-fluorobiphenylyl)-5-butylpyrimidine 6% 1-ethyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 4% 1-propyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 4% 1-ethyl-4-(2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)ethynyl)benzene 4% 1-propyl-4-(2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)ethynyl)benzene 4% 1-butyl-4-(2-(4-(2-(4-propylcyclohexyl)ethyl)phenyl)ethynyl)benzene 4% Composition example 10 2-fluoro-4-(2-(4-(4-pentylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 267) 5% 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzne (compound No. 283) 5% 4'-ethyl-4-cyanobiphenyl 7% 4'-pentyl-4-cyanobiphenyl 8% 1-cyano-4-(4-methoxymethylcyclohexyl)benzene 8% 1-cyano-4-(4-propylcyclohexyl)benzene 8% 1-pentyl-4-(4-methoxymethylcyclohexyl)cyclohexane 4% 2-(4-ethylphenyl)-5-ethylpyrimidine 3% 2-(4-ethylphenyl)-5-propylpyrimidine 3% 2-(4-ethylphenyl)-5-butylpyrimidine 3% 2-(4-(4-propylcyclohexyl)phenyl)-5-ethylpyrimidine 6% 2-(4-(4-propylcyclohexyl)phneyl)-5-propylpyrimidine 6% 1-methyl-4-(4-(4-propylcyclohexyl)cyclohexyl]benzene 7% 1-methoxy-4-(4-(4-propylcyclohexyl)cyclohexyl)benzne 4% 1-fluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 3% 1.2-difluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 5% 1,2-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1,2-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 5% Composition example 11 (for comparison purposes) 2-fluoro-4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4'-(4-propylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl) 5% 1-cyano-4-(4-(3-butenyl)cyclohexyl)benzene 7% 1-cyano-4-(4-(3-pentenyl)cyclohexyl)benzene 7% 1-cyano-4-(4-ethylcyclohexyl)benzene 5% 2-(4-ethylphenyl)-5-ethylpyrimidine 6% 2-(4-ethylphenyl)-5-propylpyrimidine 6% 2-(4-ethylphenyl)-5-butylpyrimidine 6% 1-methoxy-4-(2-(4-ethylphenyl)ethynyl)benzene 3% 1-methoxy-4-(2-(4-propylphenyl)ethynyl)benzene 3% 1-ethoxy-4-(2-(4-butylphenyl)ethynyl)benzene 3% 1-methoxy-4-(2-(4-pentylphenyl)ethynyl)benzene 3% 1-ethyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 5% 1-propyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 5% 2-(4-(4-ethylcyclohexyl)phenyl)-5-propylpyrimidine 5% 2-(4-(4-propylcydohexyl)phenyl)-5-ethylpyrimidine 5% 2-(4-(4-propylcyclohexyl)phenyl)-5-propylpyrimidine 5% 2-(4-(4-propylcydohexyl)phenyl)-5-butylpyrimidine 5% 1-propyl-4-(4-butylcyclohexyl)cyclohexane 6% Composition example 12 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 267) 5% 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 283) 5% 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 22) 5% 4-cyanophenyl 4-ethylbenzoate 10% 4-cyanophenyl 4-propylbenzoate 4% 2-(3,4-difluorophenyl)-5-propylpyrimidine 10% 2-(3,4-difluorophenyl)-5-pentylpyrimidine 10% 1-cyano-2-fluoro-4-(4-propylcyclohexyl)benzene 4% 1-cyano-2-fluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 11% 1-cyano-2-fluoro-4-(4-(4-propylcyclohexyl)cydohexyl)benzene 11% 2-(4'-fluorobiphenylyl)-5-propylpyrimidine 5% 2-(4'-fluorobiphenylyl)-5-butylpyrimidine 5% 4-fluorophenyl 4-(4-propylcyclohexyl)cyclohexanecarboxylate 5% 4-fluorophenyl 4-(4-pentylcyclohexyl)cyclohexanecarboxylate 5% Composition example 13 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 191) 5% 2'-fluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 34) 5% 2'-fluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 36) 5% 1-cyano-4-(4-(3-butenyl)cyclohexyl)benzene 7% 1-cyano-4-(4-(3-pentenyl)cyclohexyl)benzene 7% 1-cyano-4-(4-ethylcyclohexyl)benzene 7% 1-cyano-4-(4-propylcyclohexyl)benzene 7% 1-methyl-4-(2-(4-ethylphenyl)ethynyl)benzene 3% 1-methyl-4-(2-(4-hexylphenyl)ethynyl)benzene 6% 1-butyl-4-(2-(4-butylphenyl)ethynyl)benzene 3% 1-methyl-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 8% 1-propyl-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1-ethyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 5% 1-propyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 5% 1-butyl-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 5% 1-fluoro-4'-(4-ethylcyclohexyl)biphenyl 6% 1-fluoro-4'-(4-propylcyclohexyl)biphenyl 6% 1-fluoro-4'-(4-pentylcyclohexyl)biphenyl 5% Composition exmaple 14 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 191) 5% 2',6'-difluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compoundNo. 47) 5% 2',6'-difluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 49) 5% 1-cyano-2-fluoro-4-(4-ethylcyclohexyl)benzene 14% 1-cyano-2-fluoro-4-(4-propylcyclohexyl)benzene 12% 2-(4-cyanophenyl)-5-butyl-1,3-dioxane 10% 1-cyano-4-(4-methoxymethylcyclohexyl)benzene 10% 4-butoxyphenyl 4-propylcyclohexanecarboxylate 5% 4-ethoxyphenyl 4-butylcyclohexanecarboxylate 5% 4-methoxyohenyl 4-pentylcyclohexanecarboxylate 5% 1,2-difluoro-4-(4-propylcyclohexyl)cyclohexyl)benzene 10% 1-fluoro-4-(4-(4-propylcyclohexyl)benzoyloxy)benzene 8% 1-fluoro-4-(4-(4-propylcyclohexyl)carbonyloxy)benzoyloxy)benzene 6% Composition exmaple 15 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(4-pentylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 191) 5% 1-methoxy-4-(4-propylcyclohexyl)cyclohexane 7% 1-fluoro-4-(4-pentylcyclohexyl)benzene 7% 1-propoxy-4-(4-propylcyclohexyl)cyclohexane 5% 1-methoxy-4-(4-pentylcyclohexyl)cydohexane 4% 1-trifluoromethoxy-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 4% 1-difluoromethoxy-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 3% 1-trifluoromethoxy-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 5% 1-trifluoromethoxy-4-(4-(4-butylcyclohexyl)cyclohexyl)benzene 4% 1-difluoromethoxy-2,6-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 7% 1-difluorolethoxy-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 4% 1,2-difluoro-4-(2-(4-(4-propylcyclohexyl)cyclohexylethyl)benzene 7% 1-trifluoromethoxy-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 6% 3,4-difluorophenyl 4-(4-propylcyclohexyl)cyclohexanecarboxylate 4% 1-difluoromethoxy-2,6-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 10% 1,2-difluoro-4-(2-(4-(4-pentylcyclohexyl)cyclohexylethyl)benzene 8% Composition example 16 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-propylcyclohexyl)biphenyl(compound No. 1) 5% 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-pentylcyclohexyl)biphenyl(compound No. 17) 5% 2-fluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2-fluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 1-fluoro-4-(4-pentylcyclohexyl)benzene 5% 1-fluoro-4-(4-hexylcyclohexyl)benzene 5% 1-fluoro-4-(4-heplylcyclohexyl)benzene 5% 1-trifluoromethoxy-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 5% 1-trifluoromethoxy-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 7% 1,2-difluoro-4'-(4-propylcyclohexyl)biphenyl 9% 1-trifluoromethoxy-4-(4-(4-butylcyclohexyl)cyclohexyl)benzene 4% 1-trifluoromethoxy-4-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl)benzene 6% 1-trifluoromethoxy-4(4-(4-pentylcyclohexyl)cyclohexylbenzene 8% 1,2-difluoro-4'-(4-pentylcyclohexyl)biphenyl 12% 1-ethyl-2-fluoro-4'-(4-pentylcyclohexyl)biphenyl 8% 2-fluoro-4-(4-propylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl 2% 2-fluoro-4-(4-pentylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl 2% 2-fluoro-4-(4-pentylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl 2% Composition example 17 2',6'-difluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 47) 5% 2',6'-difluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 49) 5% 1-cyano-4-(4-(2-propenyl)cyclohexyl)benzene 3% 4'-butyl-4-ethylbiphenyl 3% 4'-propyl-4-cyanobiphenyl 3% 1-cyano-2-fluoro-4-(4-ethylcyclohexyl)benzene 3% 2-(3,4-difluorophenyl)-5-propylpyrimidine 3% 1-ethoxy-4-(2-(4-propylcyclohexyl)ethyl)benzene 5% 4'-pentyl-4-cyanobiphenyl 8% 4-cyanophenyl 4-propylbenzoate 3% 4-ethylphenyl 4-butylcyclohexanecarboxylate 11% 1-ethoxy-4-(2-(4-pentylycyclohexyl)ethyl)benzene 12% 4-methoxyphenyl 4-pentylcyclohexanecarboxylate 16% 4-propoxyphenyl 4-pentylcyclohexanecarboxylate 10% 2-(4-cyanophenyl)-5-(4-butylphenyl)pyrimidine 3% 1"-pentyl-4-cyanoterphenyl 5% 1-butyl-4-(2-(4-(4-pentylcycmphexyl)phenyl)elhyl)benzene 6% 2-(4-pentylphenyl)-5-(4-butylphenyl)pyrimidine 3% 1-propyl-4-(2-(4-(4-(4-pentylcyclohexyl)phenyl)phenyl)ethyl)cyclohexane 3% Composition example 18 (for comparison purposes) 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 4'-(4-pentylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5% 1,2-difluorophenyl 4-butylcyclohexanecarboxylate 11% 1,2-difluorophenyl 4-pentylcyclohexanecarboxylate 5% 1-cyano-2-fluorophenyl 4-ethylbenzoate 4% 1-cyano-2-fluoro-4-(4-(3-methoxypropyl)cyclohexyl)benzene 11% 1-cyano-2-fluorophenyl 4-propylbenzoate 4% 1-cyano-2-fluorophenyl 4-butylbenzoate 5% 1-cyano-2-fluorophenyl 4-pentylbenzoate 5% 1,2-difluorophenyl 4-(4-propylcyclohexyl)cyclohexanecarboxylate 4% 1,2-difluorophenyl 4-(4-pentylcyclohexyl)cyclohexanecarboxylate 5% 1-cyano-2-fluorophenyl 4-(4-ethylcyclohexyl)benzoate 5% 1-ethyl-4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)benzene 14% 1-cyano-2-fluorophenyl 4-(4-propylcyclohexyl)benzoate 9% 1-cyano-2-fluorophenyl 4-(4-butylcyclohexyl)benzoate 4% 1-cyano-2-fluorophenyl 4-(4-pentylcyclohexyl)benzoate 4% Composition example 19 2-fluoro-4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 267) 5% 2',6'-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 2',6'-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 5% 1-ethyl-4-(4-propylcyclohexyl)benzene 6% 1-cyano-4-(4-ethylcyclohexyl)benzene 10% 1-cyano-4-(4-propylcyclohexyl)benzene 10% 1-cyano-4-(4-butylcyclohexyl)benzene 10% 1-cyano-4-(4-pentylcyclohexyl)benzene 10% 1-cyano-4-(4-heptylcyclohexyl)benzene 10% 1-ethyl-4'-(4-propylcyclohexyl)biphenyl 12% 1-ethyl-4'-(4-pentylcyclohexyl)biphenyl 4% 1-propyl-4'-(4-propylcyclohexyl)biphenyl 3% 4-(4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl 5% Composition example 20 A composition consisting of the same components as those in Composition example 1, except that 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-propylcyclohexyl)biphenyl (compound No. 1) was replaced by 4'-(4-methoxymethylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl. Composition example 21 A composition consisting of the same components as those in composition example 8, except that 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene (compound No. 267) was replaced by 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethynyl-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene (compound No. 456). Composition example 22 A composition consisting of the same components as those in composition example 9, except that 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 283) was replaced by4-(2-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene (compound No. 457). Composition example 23 A composition consisting of the same components as those in composition example 15, except that 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl(compound No. 191) was replaced by 2',6-difluoro-4'-(2-(4-methoxymethylcyclohexyl)ethyl-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl (compound No. 445). (Example) The present invention will be described in more detail by way of Examples. Hereinafter, 1,4-cyclohexylene and 1,2-ethenylene in side chains or central linkages all represent transconformation. Further, the unit of the phase transition points are all represented by °C. Example 1 Preparation of 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-propylcyclohexyl)biphenyl (compound No. 1) (a compound of the formula (1) wherein R 1 = propyl group; X = covalent bond; Y 1 , Y 2 =hydrogen atom; ℓ = m = 1; n = 0; p = 1; ring A =cyclohexane ring; and ring B = benzene ring) A tetrahydrofuran (hereinafter abbreviated to THF) (60 mℓ) solution of 4-(4-propylcyclohexyl)bromobenzene (5.6 g, 20 mmol) prepared according to a process of Japanese patent application laid-open No. Sho 56-103120 was added to a THF (5 mℓ) solution of sufficiently dried Mg (0.54 g, 22 mmol), followed by heating the mixture under reflux for 3 hours, adding a THF solution (0.5 mol solution) of zinc chloride (44 mℓ, 22 mmol) on an ice water bath, stirring at room temperature for 30 minutes, further adding commercially available 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (6.46 g, 20 mmol) and tetrakis(triphenylphosphine) palladium (0) (680 mg), heating the mixture under reflux for 7.5 hours allowing the resulting material to cool, adding to 3N hydrochloric acid (100 mℓ), extracting with heptane (400 mℓ), washing the organic layer with water, washing with a saturated aqueous solution of sodium hydrogen carbonate, three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, subjecting the thus obtained white solids to column chromatography (using a mixed solvent of hexane/toluene (10/1) as an eluent), and recrystallizing from a mixed solvent of methanol/ethanol (9 mℓ), to obtain the captioned compound (2.18 g) (yield: 24%). Boiling point: 195 - 205°C (2 mmHg, 270 N/m 2 ) Cr 118.2°C SB 176.4°C SA 181.9°C I so The following compounds are prepared in the same manner as above: Compound No. 2. 4'-propyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 3. 4'-butyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 4. 4'-pentyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 5. 2'-fluoro-4'-propyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 6. 2'fluoro-4'-pentyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 7. 4'-propyl-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 8. 4'-pentyl-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 9. 4'-propyl-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 10. 4'-butyl-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 11. 4'-pentyl-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 14. 4'-(4-methylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 15. 4'-(4-ethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 16. 4'-(4-butylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 17. 4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl Cr 176.5°C SB 181.5°C I so 18. 4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 19. 4'-(4-hexylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 20. 4'-(4-methylcyclohexyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 21. 4'-(4-ethylcyclohexyl)-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 23. 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 26. 4'-(4-pentylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 32. 2'-fluoro-4'-(4-methylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 33. 2'-fluoro-4'-(4-ethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 34. 2'-fluora-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl Cr 91.7 (SB 90.8) SA 130.8 N 37.0 I so 35. 2'-fluoro-4'-(4-butylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 36. 2'-fluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 37. 2'-fluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 38. 2'-fluoro-4'-(4-hexylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 40. 2'-fluoro-4'-(4-ethylcyclohexyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 42. 2'-fluoro-4'-(4-butylcyclohexyl)-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 45. 2',6'-difluoro-4'-(4-methylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 46. 2',6'-difluoro-4'-(4-ethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 47. 2',6'-difluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 48. 2',6'-difluoro-4'-(4-butylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 49. 2',6'-difluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl Cr 94.3 SA 95.6 N 108.0 I so 50. 2',6'-difluoro-4'-(4-pentylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 51. 2',6'-difluoro-4'-(4-hexylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 52. 2',6'-difluoro-4'-(4-methylcyclohexyl)-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 53. 2',6'-difluoro-4'-(4-ethylcyclohexyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 55. 2'.6'-difluoro-4'-(4-butylcyclohexyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 58. 4"-propyl-4-(1,1,2,3,3,3-hexafluoropropoxy)terphenyl 59. 4"-pentyl-4-(1,1,2,3,3,3-hexafluoropropoxy)terphenyl 62. 4"-propyl-2'-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)terphenyl 66. 4"-propyl-2',6'-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)terphenyl 68. 4"-propyl-4-(1,1,2,3,3,3-hexafluoropropyl)terphenyl 69. 4"-propyl-2',6'-difluoro-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)terphenyl 70. 4"-propyl-2',6'-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)terphenyl 71. 4'-(4-(4-methylcyclohexyl)cyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 72. 2'-fluoro-4'-(4-(4-methylcyclohexyl)cyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 73. 4'-(4-(4-propylcyclohexyl)cyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 74. (2'-fluoro-4'-(4-(4-propylcyclohexyl)cyclohexyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 77. 4'-(4-(4-pentylcyclohexyl)cydohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 78. 2'-fluoro-4'-(4-(4-pentylcyclohexyl)cyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 81. 4'-(4-(4-methylcyclohexyl)cyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 82. 2'-fluoro-4'-(4-(4-propylcyclohexyl)cyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 83. 2',6'-difluoro-4'-(4-(4-propylcyclohexyl)cyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 84. 4"-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)terphenyl 86. 4"-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)terphenyl Example 2 Preparation of 4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 87) (a compound of the formula (1) wherein R 1 = propyl group; X = covalent bond; Y 1 and Y 2 : hydrogen atom; ℓ = m = 1, n = 0, p = 1; and rings A and B: cyclohexane ring) A mixture of 4-(4-propylcyclohexyl)bromocyclohexane (5.6 g, 20 mmol), prepared by reacting 4-(4-propylcyclohexyl ) cyclohexanol obtained according to methods disclosed in Japanese patent application laid-open Nos. Sho 57-64626, and Sho 57-165328, using triphenylphosphine dibromide, according to a method disclosed in Journal of the American Chemical Society, 86 , 964 (1964), zinc bromide (2.23 g, 10 mmol), lithium (280 mg), toluene (40 mℓ) and THF (3 mℓ), was irradiated by ultrasonic wave at 0°C for one hour, followed by adding to the resulting black solution, 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (6.46 g, 20 mmol) and bis(triphenylphosphine)palladium (II) chloride (600 mg), heating the mixture under reflux for 5 hours, allowing the resulting material to cool, feeding it into 3N-HCℓ. (100 mℓ), extracting with heptane, washing the organic layer with water, washing with a saturated aqueous solution of sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, subjecting the distillate to column chromatography and recrystallizing to obtain the captioned compound. Boiling point: 232 - 236°C (1 mmHg, 130 N/m 2 ). The following compounds are prepared in the same manner as above: Compound No. 88. 4-(4-methylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 89. 4-(4-methylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 90. 4-(4-ethylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 91. 4-(4-propylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 92. 4-(4-propylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 93. 4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 94. 4-(4-hexylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 95. 4-(4-(3-propenyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 96. 4-(4-(3-butenyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 97. 4-(4-butylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 98. 4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 99. 4-(4-pentylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 100. 4-(4-hexylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 101. 4-(4-heptylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Oily substance 105. 2-chloro-4-(4-butylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 108. 2-chloro-4-(4-heptylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 109. 4-(4-(4-methylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 110. 4-(4-(4-propylcyclohexyl)cyclohexy))-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 111. 4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 112. 4-(4-(4-octylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 113. 4-(4-(4-hexylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 116. 2-chloro-4-(4-(4-propylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 117. 2-chloro-4-(4-(4-pentylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 120. 4-(4-(4-(4-propylcyclonexyl)cyclonexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 121. 4-(4-(4-(4-pentylcyclohexyl)cyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 122. 4-(4-(4-(4-heptylcyclohexyl)cyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 123. 4-(4-(4-(4-nonylcyclohexyl)cyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 127. 2-chloro-4-(4-(4-(4-pentylcyclohexyl)cyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Example 3 Preparation of 4-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 128) (a compound of the formula (1) wherein R 1 = propyl group; X = -CH 2 CH 2 -; Y 1 and Y 2 = hydrogen atom; ℓ = m = 1, n = 0, p = 1; and rings A and B = cyclohexane ring) A mixture of 2-(4-(4-propylcyclohexyl)cyclohexyl)ethylbromide (6.86 g, 20 mmol) obtained by conventionally increasing the carbon number of 4-(4-propylcyclohexyl)cyclohexane carboxylic acid prepared according to a method disclosed in Angewandte Chemie 89 , 103 (1978), zinc bromide (2.23 g, 10 mmol), lithium (280 mg), toluene (50 mℓ) and THF (4 mℓ) was irradiated by ultrasonic wave at 0°C for one hour, followed by adding to the resulting black solution, 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (6.46 g, 20 mmol) and bis(triphenylphosphine)palladium (II) chloride (600 mg), heating the mixture under reflux for 5 hours, allowing the resulting material to cool, feeding it into 3N-HCℓ (100 mℓ), extracting with heptane, washing the organic layer with water, washing with a saturated sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, subjecting to column chromatography and recrystallizing, to obtain the captioned compound. Boiling Point: 238 - 245°C (1 mmHg, 130 N/m 2 ) The following compounds are prepared in the same manner as above: Compound No. 129. 4-(2-(4-ethylphenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 130. 4-(2-(4-propylphenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 131. 4-(2-(4-pentylphenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 133. 2-chloro-4-(2-(4-ethylphenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 134. 4-(2-(4-ethylcyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 135. 4-(2-(4-propylcyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 136. 4-(2-(4-pentylcyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 138. 2-chloro-4-(2-(4-ethylcyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 139. 4-(2-(4-(4-ethylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 140. 4-(2-(4-(4-butylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 141. 4-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 142. 4-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 143. 2-chloro-4-(2-(4-(4-ethylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 147. 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 148. 4-(2-(4-(4-propylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 149. 4-(2-(4-(4-butylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 150. 4-(2-(4-(4-pentylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 151. 2-chloro-4-(2-(4-(4-ethylcyclohexyl)pehnyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 154. 4-(2-(2-fluoro-4-(4-ethylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 155. 4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 156. 4-(2-(2-fluoro-4-(4-butylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 157. 4-(2-(2-fluoro-4-(4-pentylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 158. 2-chloro-4-(2-(2-fluoro-4-(4-ethylcyclohexyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 160. 4-(2-(4-(4-propylphenyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 161. 4-(2-(4-(4-pentylphenyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 163. 2-chloro-4-(2-(4-(4-propylphenyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 164. 2-methyl-4-(2-(4-(4-propylphenyl)phenyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 166. 4-(2-(4-(4-propylphenyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 167. 4-(2-(4-(4-pentylphenyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 168. 2-methyl-4-(2-(4-(4-propylphenyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 172. 2-chloro-4-(2-(4-(2-fluoro-4-propylphenyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 173. 4'-(2-(4-propylphenyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 177. 4'-(2-(4-propylphenyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 178. 4'-(2-(4-propylphenyl)ethyl-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 179. 4'-(2-(4-propylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 183. 4'-(2-(4-propylphenyl)ethyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 184. 2'-fluoro-4'-(2-(4-propylphenyl)ethyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 185. 4'-(2-(4-(4-propylcyclohexyl)phenyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 188. 4'-(2-(4'-propylbiphenylyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 189. 4'-(2-(4'-propylbiphenylyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl Example 4 Preparation of 4'-(2-(4-propylcyclohexyl)ethyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (compound No. 191) (a compound of the formula (1), wherein R 1 = propyl group; X = -CH 2 CH 2 -; Y 1 and Y 2 = hydrogen atom; ℓ= 1, m=0, p = 1; ring A: cyclohexane ring; and ring C: benzene ring) A hexane solution of n-butyllithium (12.5 mℓ, 20 mmol) (1.60 mol solution) was dropwise added to a THF (80 mℓ) solution of 4-(2-(4-propylcyclohexyl)ethyl)iodobenzene (5.94 g, 16.7 mmol) prepared according to the method disclosed in the Journal of Practical Chemistry, 320 , 191 (1978), at -50°C or lower, followed by stirring at the same temperature for 2 hours, adding a THF solution (0.5 mol solution) of zinc chloride (40 mℓ, 20 mmol), stirring the mixture at room temperature for 45 minutes, further adding 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (6.46 g, 20 mmol) and tetrakis(triphenylphosphine)palladium (0) (5,000 mg), heating the mixture under reflux for 2.5 hours, allowing the resulting material to cool, feeding it into 3-N HCℓ (400 mℓ), extracting with toluene (200 mℓ), washing the organic layer with water, washing with a saturated aqueous solution of sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, subjecting the residue to column chromatography (eluent: hexane), and recrystallizing from a mixed solvent (10 mℓ) of methanol with ethanol, to obtain the captioned compound (2.39 g) (yield: 30%). Cr 139.7°C (SB 139.5°C) SA 144.7°C N 146.5°C I so The following compounds are prepared in the same manner as above: 192. 4'-(2-(4-butylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 193. 4'-(2-(4-pentylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 194. 4'-(2-(4-hexylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 196. 4'-(2-(4-butylcyclohexyl)ethyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 198. 4'-(2-(4-hexylcyclohexyl)ethyl)-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 199. 4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 200. 4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 201. 4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 202. 4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 206. 4'-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl Example 5 Preparation of 4-(2-(4-(4-propylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 211) (a compound of the formula (1) wherein R 1 = propyl group; X = -CH=CH-; Y 1 and Y 2 = hydrogen atom; ℓ = m = 1, n = 0, p = 1; and rings A and B = cyclohexane ring) An ultrasonic wave was irradiated at 0°C for onr hour, to a mixture of 2-(4-(4-propylcyclohexyl)cyclohexyl)iodized ethenyl (6.82 g, 20 mmol) prepared according to the method disclosed in Journal of the American Chemical Society, 95 , 5786 (1973), zinc bromide (2.23 g, 10 mmol), lithium (280 mg), toluene (50 mℓ) and THF (4 mℓ), followed by adding to the resulting black solution, 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (6.46 g, 20 mmol) and bis(triphenylphosphine)palladium (II) chloride (600 mg), heating the mixture under reflux for 5 hours, allowing the resulting material to cool, feeding it into 3N-HCℓ (100 mℓ), extracting with heptane, washing the organic layer with water, washing with a saturated aqueous solution of sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, subjecting the distillate to column chromatography and recrystallizing, to obtain the captioned compound. Boiling point: 221 - 228°C (1 mmHg, 130 N/m 2 ) The following compounds are prepared in the same manner as above: Compound No. 212. 4-(2-(4-ethylphenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 213. 4-(2-(4-propylphenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Oily substance 214. 4-(2-(4-pentylphenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 216. 2-chloro-4-(2-(4-ethylphenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 217. 4-(2-(4-ethylcyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 218. 4-(2-(4-propylcyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 219. 4-(2-(4-pentylcyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 221. 2-chloro-4-(2-(4-ethylcyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 222. 4-(2-(4-(4-ethylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 223. 4-(2-(4-(4-butylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 224. 4-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 225. 4-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 226. 2-chloro-4-(2-(4-(4-ethylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy) benzene 229. 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 230. 4-(2-(4-(4-propylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 231. 4-(2-(4-(4-butylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluordpropoxy)benzene 232. 4-(2-(4-(4-pentylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 233. 2-chloro-4-(2-(4-(4-ethylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 235. 4-(2-(2-fluoro-4-(4-ethylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 236. 4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 237. 4-(2-(2-fluoro-4-(4-butylcyclohexyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 238. 4-(2-(2-fluoro-4-(4-pentylcyclohexyl)phenyl)ethenyl)(1,1,2,3,3,3-hexafluoropropoxy)benzene 239. 2-chloro-4-(2-(2-fluoro-4-(4-ethylcyclohexyl)phenyl)-ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 240. 2-fluoro-4-(2-(2-fluoro-4-(4-propylcyclohexyl)phenyl)-ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 241 4-(2-(4-(4-propylphenyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 242. 4-(2-(4-(4-pentylphenyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 244. 2-chloro-4-(2-(4-(4-propylphenyl)phenyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 245. 2-methyl-4-(2-(4-(4-propylphenyl)phenyl)ethenyl-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 247. 4-(2-(4-(4-propylphenyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 248. 4-(2-(4-(4-pentylphenyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 249. 2-methyl-4-(2-(4-(4-propylphenyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 253. 2-chloro-4-(2-(4-(2-fluoro-4-propylphenyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 254. 4'-(2-(4-propylcyclohexyl)ethenyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 255. 4'-(2-(4-butylcyclohexyl)ethenyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 256. 4'-(2-(4-pentylcyclohexyl)ethenyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 257. 4'-(2-(4-hexylcyclohexyl)ethenyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 259. 4'-(2-(4-butylcyclohexyl)ethenyl)-3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 261. 4'-(2-(4-hexylcyclohexyl)ethenyl)-3-methyl-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 262. 4'-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethenyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl Example 6 Preparation of 4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (compound No. 267) (a compound of the formula (1) wherein R = ethyl group; X = -C=C-; Y 1 and Y 2 =hydrogen atom; ℓ = m = 1, n = 0, p = 1; ring A = cyclohexane ring and ring B = benzene ring) A hexane solution of n-butyllithium (6.25 mℓ, 10 mmol) (1.60 mol solution) was dropwise added at -40°C or lower, to a THF (5 mℓ) solution of 4-(4-propylcyclohexyl)phenylacetylene (2.12 g, 10 mmol), prepared according to the method of Tetrahedron Letters, 2881 (1965), followed by stirring at the same temperature for 20 minutes, adding a THF solution of zinc chloride (20 mℓ, 10 mmol) (0.5 mol solution), stirring the mixture at room temperature for 30 minutes, further adding 4-(1,1,2,3,3,3-hexafluoropropoxy)bromobenzene (3.23 g, 10 mmol) and tetrakis(triphenylphosphine)palladium (0) (500 mg), heating the mixture under reflux for 3.5 hours, allowing the resulting material to cool, feeding it into 3N-HCℓ (100 mℓ), extracting with toluene (100 mℓ), washing the organic layer with water, washing with a saturated sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, subjecting the residue to column chromatography (eluent: heptane), and recrystallizing from a mixed solvent of methanol with ethanol (15 mℓ), to obtain the captioned compound (2.9 g) (yield: 64%). Cr 1 93.0°C Cr 2 111.9°C SA 181.4°C N 192.3°C I so The following compounds are prepared in the same manner as above: 268. 4-(2-(4-propylphenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Cr 68.7°C I so 269. 4-(2-(4-butylphenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 270. 4-(2-(4-butylphenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 271. 4-(2-(4-pentyloxyphenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 272. 2-fluoro-4-(2-(4-propylphenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 274. 4-(2-(4-propylcyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 275. 4-(2-(4-butylcyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 276. 4-(2-(4-pentyloxycyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 279. 4-(2-(4-(4-propylphenyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 280. 4-(2-(4-(4-pentylphenyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 281. 4-(2-(4-(4-propoxyphenyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 283. 4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 285. 4-(2-(4-(4-pentylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 289. 2,6-difluoro-4-(2-(4-(4-ethylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 291. 4-(2-(2-fluoro-4-(4-propoxycyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 293. 4-(2-(4-(4-ethylphenyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 294. 4-(2-(4-(4-pentylphenyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 295. 4-(2-(4-(4-propoxyphenyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-haxafluoropropoxy)benzene 297. 4-(2-(2-fluoro-4-(4-propoxyphenyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (wherein fluorine atom on the cyclohexane ring is present in an axial position) 299. 4-(2-(4-(4-ethylcyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 300. 4-(2-(4-(4-pentylcyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 301. 4-(2-(4-(4-propoxycyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 303. 4-(2-(2-fluoro-4-(4-propoxycyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene (wherein fluorine atom on the cyclohexane ring is present in an axial position) 305. 4'-(2-(4-propylphenyl)ethynyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 306. 4'-(2-(4-butylphenyl)ethynyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 307. 4'-(2-(4-pentylphenyl)ethynyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 309. 4'-(2-(2-fluoro-4-butylphenyl)ethynyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 310. 4-(4-(2-(4-propylphenyl)ethynyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 311. 4-(4-(2-(4-butylphenyl)ethynyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 312. 4-(4-(2-(4-pentylphenyl)ethynyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 314. 4-(4-(2-(2-fluoro-4-butylphenyl)ethynyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Example 7 Preparation of 4'-(4-propylbenzyloxy)-1-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (compound No. 315) (a compound of the formula (1) wherein R 1 = propyl group; X = -CH 2 O-; Y 1 and Y 2 : hydrogen atom; ℓ = n = 1, m = 0, p = 1; rings A and C: benzene ring) A THF (40 mℓ) solution of 4'-hydroxy-1-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (4.46 g, 10 mmol) prepared from commercially available bisphenol and 1,1,2,3,3,3-hexafluoroiodopropane was dropwise added to a mixture of sodium hydride (240 mg, 10 mmol) with THF (20 mℓ) under ice cooling, followed by stirring the mixture for 30 minutes, adding to the mixture, a THF (10 mℓ) solution of 4-propylbenzyl bromide (2.13 g, 10 mmol), stirring the mixture at room temperature for 3 hours, feeding the resulting material into 3N-HCℓ, extracting with toluene (100 mℓ), washing with water, then with a saturated aqueous solution of sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulphate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, recrystallizing the distillate under reduced pressure, subjecting it to column chromatography (eluent: heptane), and recrystallizing from ethanol to obtain the captioned compound. Boiling point: 260 - 265°C (1 mmHg, 130 N/m 2 ) The following compounds are prepared in the same manner as above: Compound No. 316. 4-(ethylbenzyloxy)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 318. 4-(4-propylcyclohexylmethyloxy)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene 320. 4'-(4-ethylbenzyloxy)-1-(1,1,2,3,3,3-hexatluoropropoxy)biphenyl 321. 4'-(4-ethylbenzyloxy)-2-fluoro-1-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 322. 4'-(4-ethylcyclohexylmethyloxy)-1-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl 325. 4'-(4-propylcyclohexylmethyloxy)-2,6-difluoro-1-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 326. 4-(4-(4-propylcyclohexyl)cyclohexylmethyloxy)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene Example 8 Preparation of 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)-1-(4-pentylcyclohexyl)benzene (compound No. 328) (a compound of the formula (1) wherein R 1 = pentyl group; X = -OCH 2 -; Y 1 and Y 2 hydrogen atom; ℓ=m=1, n=0, p = 1; ring A = cyclohexyl ring; and ring B = benzene ring) A THF (30 mℓ) solution of 4-(4-propylcyclohexyl)phenol (2.19 g, 10 mmol) prepared according to Japanese patent application laid-open Nos. Sho 57-64626 and Sho 57-165328, was dropwise added to a mixture of sodium hydride (240 mg, 10 mmol) with THF (20 mℓ). stirring the mixture under ice-cooling for 30 minutes, followed by adding a THF (10 mℓ) solution of 4-(1,1,2,3,3,3-hexafluoropropoxy)benzyl chloride (2.92 g, 10 mmol), prepared from commercially available 4-hydroxybenzyl chloride and 1,1,2,3,3,3-hexafluoroiodopropane, stirring the mixture at room temperature for 3 hours. feeding the resulting material into 3N-HCℓ, extracting with toluene (100 mℓ), washing with water, washing with a saturated aqueous solution of sodium hydrogen carbonate, further three times washing with water, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, distilling the residue under reduced pressure, subjecting the distillate to column chromatography (eluent: heptane) and recrystallizing from ethanol, to obtain the captioned compound. Boiling point: 238 - 244°C (1 mmHg, 130 N/m 2 ) The following compounds are prepared in the same manner as above: Compound No. 329. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)propylbenzene 331. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)-3-fluoro-1-pentylbenzene 333. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)-1-propylcyclohexane 336. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)-1-(4-(4-propylcyclohexyl)phenyl)benzene 337. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)benzyloxy)-1-(4-(4-propylphenyl)cyclohexyl)benzene 338. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)cyclohexylmethyloxy-1-propylcyclohexane 340. 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)benzyloxy-1-propylcyclohexane 343. 4-(3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl)benzyloxy-1-propylcyclohexane Example 9 Preparation of 4'-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)biphenylyl 4-propylcyclohexylcarboxylate (compound No. 344) (a compound of the formula (1) wherein R 1 = propyl group; X -CO-O-; Y 1 and Y 2 = hydrogen atom; ℓ = n = 1, m = 0, p = 1; and ring A = cyclohexane ring and ring C = benzene ring) Dicyclohexylcarbodiimide (2.06 g, 10 mmol) and dimethylaminopyridine (122 mg, 1 mmol) were added to a mixture of 4'-hydroxy-1-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (4.46 g, 10 mmol) prepared in Example 7, 4-propylcyclohexanecarboxylic acid (1.70 g, 10 mmol) and dichloromethane (30 mℓ), followed by stirring the resulting mixture at room temperature overnight, filtering off the insolubles, distilling off the solvent under reduced pressure, subjecting the residue to column chromatography (eluent: heptane) and recrystallizing from ethanol, to obtain the captioned compound. The following compounds are obtained in the same manner as above. Compound No. 345. 4'-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)biphenylyl 4-pentylcyclohexylcarboxylate 348. 4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 4-propylcyclohexylcarboxylate Oily substance 349. 4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl 4-pentylcyclohexylcarboxylate 352. 3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-pentylcyclohexylcarboxylate Example 10 Preparation of 4-(4-propylcyclohexyl)phenyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate (compound No. 353) (a compound of the formula (I), wherein R 1 =propyl group; X = -O-CO-; Y 1 and Y 2 hydrogen atom; ℓ=m=1, n=0,p= 1; and ring A = cyclohexane ring; and ring B = benzene ring) A mixture of 4-(4-propylcyclohexyl)phenol prepared in Example 8, 4-(4-propylcyclohexyl)phenyl 4-hydroxybenzoate (3.39 g. 10 mmol) prepared from 4-hydroxybenzoic acid according to the method of Tetrahydrogen Letters, 3453 (1971) and 1,1,2,3,3,3-hexafluoroiodopropane (5.50 g, 20 mmol), was stirred at 60°C, under 10 atm, for 3 hours, followed by allowing the resulting material to cool, distilling off the solvent, subjecting the residue to column chromatography (eluent: haptane) and recrystallizing from ethanol, to obtain the captioned compound. The following compounds are prepared in the same manner as above: Compound No. 354. 4-(4-pentylcyclohexyl)phenyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 357. 4-(4-propylcyclohexyl)phenyl 3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)benzoate 359. 4-propylcyclohexyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 360. 4-pentylcyclohexyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 362. 4-propylphenyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 363. 4-propylphenyl 4-(1,1,2,3,3,3-hexafluoropropyl)benzoate 364. 4-pentylphenyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 365. 4-propylphenyl 3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 367. 4-(4-propylcyclohexyl)cyclohexyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 368. 4-(4-pentylcyclohexyl)cyclohexyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 369. 4-(4-propylcyclohexyl)cyclohexyl 3-chloro-4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate 371. 4-propylcyclohexyl 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)benzoate 372. 4-pentylcyclohexyl 4-(4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)benzoate Example 11 Preparation of 4'-(4-methoxymethylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl (a compound of the formula (I) wherein R 1 = methoxymethyl group; X = covalent bond; Y 1 =hydrogen atom; Y 2 = fluorine atom; = = m = 1, n = 0, p = 1; ring A = cyclohexane ring; and ring B = benzene ring) A hexane solution of n-butyllithium (12.3 mℓ, 20 mmol) (1.63 mol solution) was added to a THF (60 mℓ) solution of 4-(4-methoxymethylcyclohexyl)-1-iodobenzene (5.51 g, 17 mmol) at -50°C in a nitrogen atmosphere, followed by stirring the mixture at the same temperature for 90 minutes, adding a THF solution (0.5 mol) of zinc chloride (40 mℓ, 20 mmol), stirring the mixture at room temperature for one hour, further adding tetrakis(triphenylphosphine)palladium (0) (0.5 g) and 4-(1,1,2,3,3,3-hexafluoropropoxy)-3-fluorobromobenzene (6.82 g, 20 mmol), heating the mixture under reflux for 5 hours, allowing the resulting material to cool, adding toluene (200 mℓ) to the resulting reaction mixture, washing the organic layer successively with 3N-HCℓ (200 mℓ), water (200 mℓ) and a saturated aqueous solution of sodium hydrogen carbonate (200 mℓ), next three times washing with water (200 mℓ), drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, subjecting the residue to column chromatography (eluent: heptane/toluene = 1:1), and recrystallizing from heptane, to obtain the captioned compound (1.47 g) (yield: 16%). Cr 86.4 SA 134.2 N 143.2 I so The following compounds are prepared in the same manner as above: Compound No. 376. 4-(4-methoxymethylcyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 377. 4'-(4-methoxymethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 378. 4'-(4-ethoxymethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 379. 4'-(4-propoxymethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 380. 4'-(4-methoxyethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 381. 4'-(4-ethoxyethylcyclohexyl)-4- (1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 392. 4-(4-methoxymethoxycyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 393. 4'-(4-methoxymethoxycyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 394. 4'-(4-ethoxymethoxycyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 395. 4'-(4-methoxyethoxycyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 401. 4'-(4-methoxymethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 402. 4'-(4-ethoxymethylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 403. 4'-(4-methoxymethylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 404. 4'-(4-ethoxymethylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 405. 4'-(4-methoxymethylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 406. 4'-(4-ethoxymethylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 407. 4'-(4-methoxymethoxycyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 408. 4'-(4-ethoxymethoxycyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 409. 4'-(4-methoxymethoxycyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 410. 4'-(4-ethoxymethoxycyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 411. 4'-(4-methoxymethoxycyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 412. 4'-(4-ethoxymethoxycyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl In the same manner as in Example 5, Example 6 and Example 9, the following compounds of compound Nos. 413-428, 429-433, 434-449, 450-461 and 462-485, can be prepared: Compound No. 413. 4-(4-(4-methoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 414. 4-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 415. 4-(4-(4-methoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)-2-fluorobenzene 417. 4-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 418. 4-(4-(4-ethoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 421. 4-(4-(4-methoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 422. 4-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 423. 4-(4-(4-methoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2-fluorobenzene 424. 4-(4-(4-methoxymethylcyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2,4-difluorobenzene 425. 4-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 426. 4-(4-(4-ethoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 427. 4-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2-fluorobenzene 428. 4-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2,4-difluorobenzene 429. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethyl-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 430. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 431. 4-(2-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)ethyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 434. 4'-(2-(4-(4-methoxymethylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 435. 4'-(2-(4-ethoxymethylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 437. 2',6'-difluoro-4'-(2-(4-methoxymethylcyclohexyl)ethyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 438. 4'-(2-(4-methoxymethoxycyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 439. 4'-(2-(4-ethoxymethoxycyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyloxy)bipheny) 442. 4'-(2-(4-methoxymethylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 443. 4'-(2-(4-ethoxymethylcyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 444. 4'-(2-(4-methoxymethylcyclohexyl)ethyl)-3,5-diflroro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 445. 2',6'-difluoro-4'-(2-(4-methoxymethylcyclohexyl)ethyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 446. 4'-(2-(4-methoxymethoxycyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 447. 4'-(2-(4-ethoxymethoxycyclohexyl)ethyl)-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 448. 4'-(2-(4-methoxymethoxycyclohexyl)ethyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 449. 2',6'-difluoro-4'-(2-(4-methoxymethoxycyclohexyl)ethyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)biphenyl 450. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 451. 4-(2-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 454. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 455. 4-(2-(4-(4-methoxymethyloxycyclohexyl)cyclohexyl)ethenyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2,6-difluorobenzene 456. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyloxy)benzene 457. 4-(2-(4-(4-methoxymethoxycyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-herafluoropropyloxy)benzene 460. 4-(2-(4-(4-methoxymethylcyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyl)benzene 461. 4-(2-(4-(4-methoxymethyloxycyclohexyl)cyclohexyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropyl)-2,6-difluorobenzene 462. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-methoxymethylcyclohexylcarboxylate 463. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-ethoxymethylcyclohexylcarboxylate 464. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-methoxymethoxycyclohexylcarboxylate 465. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-ethoxymethoxycyclohexylcarboxylate 466. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-methoxyethoxycyclohexylcarboxylate 467. 4-(1,1,2,3,3,3-hexafluoropropyloxy)phenyl 4-ethoxyethoxycyclohexylcarboxylate 470. 4-(1,1,2,3,3,3-hexatluoropropyloxy)biphenylyl 4-methoxymethylcyclohexylcarboxylate 471. 4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 4-ethoxymethylcyclohexylcarboxylate 472. 4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 4-methoxymethoxycyclohexylcarboxylate 473. 4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 4-ethoxymethoxycyclohexylcarboxylate 474. 4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 4-methoxyethoxycyclohexylcarboxylate 475. 4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl 4-ethoxyethoxycyclohexylcarboxylate 478. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-methoxymethylcyclohexylcarboxylate 479. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-ethoxymethylcyclohexylcarboxylate 480. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-methoxymethoxycyclohexylcarboxylate 481. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-ethoxymethoxycyclohexylcarboxylate 482. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-methoxyethoxycyclohexylcarboxylate 483. 4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-ethoxyethoxycyclohexylcarboxylate 484. 3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-methoxymethylcyclohexylcarboxylate 485. 3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropyl)phenyl 4-methoxymethylcyclohexylcarboxylate Example 12 (Use example 1) A lqiuid crystal composition A consisting of the following composition was prepared as a base mixture: 1,2-difluoro-4-(4-(4-ethylcyclohexyl)cyclohexyl)benzene 9.09% 1,2-difluoro-4-(4-(4-propylcyclohexyl)cyclohexyl)benzene 9.09% 1,2-difluoro-4-(4-(4-pentylcyclohexyl)cyclohexyl)benzene 9.09% 1,2-difluoro-4-(4-(2-(4-ethylcyclohexyl)ethyl)cyclohexyl)benzene 18.18% 1,2-difluoro-4-(4-(2-(4-propylcyclohexyl)ethyl)cyclohexyl)benzene 9.09% 1,2-difluoro-4-(4-(2-(4-pentylcyclohexyl)ethyl)cyclohexyl)benzene 18.18% 3,4-difluoro-4'-(4-ethylcyclohexyl)biphenyl 9.09% 3,4-difluoro-4'-(4-propylcyclohexyl)biphenyl 9.09% 3,4-difluoro-4'-(4-pentylcyclohexyl)biphenyl 9.09% The values of the physical properties of this composition were as follows: Clearing point: 100.2°C, Δn: 0.093, Δc:5.1, viscosity η at 20° C: 24.5 cP, and threshold voltage in a cell thickness of 8 µm: 2.15V. Next, 4'-(1,1,2,3,3,3-hexafluoropropoxy)-4-(4-propylcyclohexyl)biphenyl (compound No. 1) (20%) was added to the above composition A (80%) to prepare a composition B 1 , followed by determining its values of physical properties. The results were as follows (the values within the parenthese refer to calculated extraporated values; this applies to those of the following Examples): Clearing point: 109.1°C (144.7°C), Δn: 0.103 (0.143), ▵ε: 4.9, threshold voltage in a cell thickness of 8.8 µm: 2.35V. Example 13 (Use exmaple 2) (for comparison purposes) Example 11 was repeated except that compound No. 1 was replaced by 4'-(4-propylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (compound No. 22), to prepare composition B 2 . The values of physical properties of this composition were as follows: Clearing point: 106.1°C (129.7°C), Δn: 0.102 (0.138) ▵ε: 5.2, viscosity at 20°C, η:26.9 cP, and threshold voltage in a cell thickness of 8.8 µm: 2.28 V. Example 14 (Use example 3) (for comparison purposes) Example 11 was repeated except compound No. 1 was replaced by 4'-(4-propylcyclohexyl)-3,5-difluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (compound No. 28), to prepare a composition B 3 . The values of physical properties of this composition B 3 were as follows: Clearing point: 102.8°C (113.2°C), Δn: 0.101 (0.133), Δε:5.6, viscosity η at 20°C: 28.4 cP; and threshold voltage in a cell thickness of 8.7 µm: 2.11 V. Example 15 (Use example 4) Example 11 was repeated except that compound No. 1 was replaced by 2'-fluoro-4'-(4-propylcyclohexyl)-4-(1,1,2,3,3,3-hexafluoropropoxy)biphenyl (compound No. 34), to prepare a composition B 4 . The values of physical properties of this composition B 4 were as follows: Clearing point: 102.8°C (113.2°C). Δn: 0.100 (0.129), ▵ε: 5.0 (4.6), viscosity at 20°C η: 27.4 (39.1) cP, and threshold voltage in a cell thickness of 8.7 µm: 2.26 V. Example 16 (Use example 5) ( for comparison purposes) Example 11 was repeated except that compound No. 1 was replaced by 2,6-difluoro-4-(2-(4-(4-propylcyclohexyl)phenyl)ethynyl)-1-(1,1,2,3,3,3-hexafluoropropoxy)benzene to prepare a composition B 5 . The values of physical properties of this composition B 5 were as follows: Clearing point: 106.5°C (131.7°C), Δn: 0.112 (0.187). Δε: 5.9 (9.1), viscosity at 20°C, η: 29.9 (51.6) cP, and threshold voltage in a cell thickness of 8.7 µm: 2.11 V. Example 17 (Use example 6) A liquid crystal composition C consisting of the following composition was prepared as a base mixture: 4-(4-propylcyclohexyl)benzonitrile 30% 4-(4-pentylcyclohexyl)benzonitrile 40% 4-(4-heptylcyclohexyl)benzonitrile 30%. The values of physical properties of this composition C were as follows: Clearing point: 52.3°C, ▵n: 0.119, ▵c: 10.7, viscosity at 20°C η: 21.7 m Pas, and threshold voltage in a cell thickness of 9.7 µm: 1.60V. Next, 4'-(4-methoxymethylcyclohexyl)-3-fluoro-4-(1,1,2,3,3,3-hexafluoropropyloxy)biphenyl (20%) was added to the composition C (80%), to prepare a composition B 6 , followed by determining its values of physical properties. The values were as follows (the values inside the parenthes refer to extrapolated values): Clearing point: 56.3°C (79.0°C), Δn: 0.121 (0.130), Δε: 10.5 (9.4), viscosity at 20°C η: 27.1 (57.6)m Pas, and threshold voltage in a cell thickness of 8.7 µm: 1.51 V. Effectiveness of the Invention As shown in Examples, the compounds provided by the present invention have the following characteristics: 1) a large Δn, 2) a low viscosity, 3) a high chemical stability and a high VHR, 4) since the clearing point and the compativility are very high, reduction in the nematic liquid phase of the composition does not occur, and 5) a very high Δε. Thus, when the compound of the present invention is used as a component of a liquid crystal composition, it is possible to provide a liquid crystal composition having a large Δn, a low viscosity and a high voltage retention and exhibiting a nematic liquid crystal phase within a broad temperature range. In particular, it is possible to provide a liquid crystal composition suitable to use for TFT, since it has a very high ▵ε.

Claims: A liquid crystalline compound expressed by the formula (1) wherein R 1 represents an alkyl group of 1 to 12 carbon atoms and one CH 2 group or two CH 2 groups not adjacent to each other in said alkyl group may be replaced by group(s) selected from among oxygen atom, -CO-group, -O-CO-group, -CO-O-group and -CH=CH-group; X represents a covalent bond, -CH 2 CH 2 -, -CH=CH-, -C≡C-, -CH 2 O-, -OCH 2 -, -CO-O- or -O-CO-; Y 1 and Y 2 each independently represent hydrogen atom, fluorine atom, chlorine atom or methyl group; rings A, B and C each independently represent a benzene ring or a cyclohexane ring and these rings may be substituted by halogen atom(s) or methyl group(s); and ℓ, m, n and p each independently represent 1 or 0, but ℓ+m is one or more, with the proviso that when p = 1, then weither Y 1 nor Y 2 represent a fluorine atom. A liquid crystalline compound according to claim 1, wherein R 1 represents an alkyl group of 1 to 12 carbon atoms and said one CH 2 group or two CH 2 groups not adjacent to each other in said alkyl group may be replaced by oxygen atom or -CH=CH- group; X represents a covelent bond, -CH 2 CH 2 - or -C≡C-; and Y 1 and Y 2 each independently represent hydrogen atom or fluorine atom. A liquid crystalline compound according to claim 2, wherein said R 1 represents an alkyl group of 1 to 12 carbon atoms. A liquid crystalline compound according to claim 3, wherein said ring C represents a benzene ring or benzene ring substituted by halogen atom or methyl group. A liquid crystalline compound according to claim 3, wherein said ring C represents a cyclohexane ring or a cyclohexane ring substituted by halogen atom or methyl group. A liquid crystalline compound according to claim 2, wherein said R 1 represents an alkyl group of 1 to 12 carbon atoms and said one CH 2 group or two CH 2 groups not adjacent to each other in said alkyl group is replaced by oxygen atom. A liquid crystalline compound according to claim 6, wherein said ring C represents benzene ring or a benzene ring substituted by halogen atom or methyl group. A liquid crystalline compound according to claim 6, wherein said ring C represents cyclohexane ring or a cyclohexane ring substituted by halogen atom or methyl group. A liquid crystal composition comprising at least two components at least one of which is a liquid crystalline compound set forth in any one of claims 1 to 8.

Inventors: FUJITA ATSUKO, GOTO YASUYUKI, MATSUI SHUICHI, MIYAZAWA KAZUTOSHI, TOMI YOSHITAKA, FUJITA, ATSUKO, GOTO, YASUYUKI, MATSUI, SHUICHI, MIYAZAWA, KAZUTOSHI, TOMI, YOSHITAKA
Applicants: CHISSO CORP, CHISSO CORPORATION
Application year: 1994
Main classification: C07C22
IPC codes: C07C25, C07C69, C09K19, C07C43, C07C22, G02F1